para-Bridged Symmetrical Pillar[5]arenes: Their Lewis Acid Catalyzed Synthesis and Host–Guest Property

Condensation of 1,4-dimethoxybenzene (DMB) with paraformaldehyde in the presence of BF3·O(C2H5)2 gave novel para-bridged pentacyclic pillar DMB (DMpillar[5]arene). Moreover, para-bridged pentacyclic hydroquinone (pillar[5]arene) was prepared. Pillar[5]arene formed 1:1 host–guest complexes with dialk...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-04, Vol.130 (15), p.5022-5023
Main Authors: Ogoshi, Tomoki, Kanai, Suguru, Fujinami, Shuhei, Yamagishi, Tada-aki, Nakamoto, Yoshiaki
Format: Article
Language:English
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Summary:Condensation of 1,4-dimethoxybenzene (DMB) with paraformaldehyde in the presence of BF3·O(C2H5)2 gave novel para-bridged pentacyclic pillar DMB (DMpillar[5]arene). Moreover, para-bridged pentacyclic hydroquinone (pillar[5]arene) was prepared. Pillar[5]arene formed 1:1 host–guest complexes with dialkyl viologen and alkyl pyridinium derivatives. However, pillar[5]arene did not form complexes with the diadamantyl viologen derivative since a bulky adamantyl group was unable to thread the cavity of pillar[5]arene.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja711260m